N-phenylsulfonyl-N&#39;-triazinylureas

ABSTRACT

N-Phenylsulfonyl-N&#39;-pyrimidinylureas and N-phenylsulfonyl-N&#39;-triazinylureas of the general formula I ##STR1## wherein A is a radical of the formula --C.tbd.C--R, 
     m is 1 or 2, 
     Z is oxygen or sulfur, 
     R is hydrogen; unsubstituted or substituted, branched or unbranched C 1  -C 9  alkyl; unsubstituted or substituted C 3  -C 9  cycloalkyl; unsubstituted or substituted phenyl; or an unsubstituted or substituted 5- or 6-membered aromatic heterocyclic ring, 
     R 1  is hydrogen, halogen, C 1  -C 5  alkyl, C 2  -C 5  alkenyl or a radical --Y--R 5 , 
     R 2  is hydrogen, halogen, C 1  -C 5  alkyl, C 2  -C 5  alkenyl, C 1  -C 4  haloalkyl, or a radical --Y--R 5 , --COOR 6 , --NO 2  or --CO--NR 7  --R 8 , 
     R 3  and R 4 , each independently of the other, are hydrogen, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, C 1  -C 4  alkylthio, C 1  -C 4  haloalkyl, C 1  -C 4  haloalkoxy, C 1  -C 4  haloalkylthio, halogen, C 2  -C 5  alkoxyalkyl, --NR 9  R 10  or --O--CH 2  --CH 2  --NR 9  R 10 , 
     R 5  and R 6 , each independently of the other, are C 1  -C 5  alkyl, C 2  -C 5  alkenyl or C 2  -C 6  alkynyl, C 1  -C 5  haloalkyl, C 2  -C 5  haloalkenyl or C 2  -C 6  alkoxyalkyl, 
     R 7  and R 8 , each independently of the other, are hydrogen, C 1  -C 5  alkyl, C 2  -C 5  alkenyl or C 2  -C 6  alkynyl, 
     R 9  is hydrogen, methyl or ethyl, 
     R 10  is hydrogen, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, methoxymethyl, cyanomethyl, cyanoethyl, C 3  -C 5  alkenyl or C 3  -C 6  alkynyl, and 
     Y is oxygen, sulfur, a sulfinyl or sulfonyl bridge 
     and the salts of these compounds with amines, alkali metal bases or alkaline earth metal bases or with quaternary ammonium bases, have good preemergence and postemergence selective herbicidal and growth regulating properties.

This is a divisional of application Ser. No. 496,326 filed on May 19,1983, now U.S. Pat. No. 4,537,618.

The present invention relates to novelN-phenylsulfonyl-N'-pyrimidinylureas andN-phenylsulfonyl-N'-triazinylureas having herbicidal and plantgrowth-regulating properties, to the production thereof, to compositionscontaining them, and to the use thereof for controlling weeds, inparticular selectively, in crops of useful plants, or for regulating andinhibiting plant growth. The invention also relates to novelphenylsulfonamides prepared as intermediates.

The N-phenylsulfonyl-N'-pyrimidinylureas andN-phenylsulfonyl-N'-triazinylureas of this invention, and the saltsthereof, have the general formula I ##STR2## wherein

A is a radical of the formula --C.tbd.C--R,

m is 1 or 2,

E is the methine group or nitrogen,

Z is oxygen or sulfur,

R is hydrogen; branched or unbranched C₁ -C₉ alkyl which isunsubstituted or substituted by halogen, hydroxyl, C₁ -C₄ alkoxy, C₁ -C₄alkylthio, C₁ -C₄ haloalkoxy, C₃ -C₉ cycloalkyl, cyano, --COOR₆, --CONR₇R₈ or by phenyl which is in turn unsubstituted or substituted byhalogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, nitro, cyano or trifluoromethyl;or is C₃ -C₉ cycloalkyl which is unsubstituted or substituted byhalogen, hydroxyl, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ alkylthio, cyano,--COOR₆, --CONR₇ R₈ ; or is phenyl or phenyl substituted by halogen,nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ alkylthio,trifluoromethyl, --COOR₆ or --CONR₇ R₈ ; or is a 5- or 6-memberedaromatic heterocyclic ring which is unsubstituted or substituted byhalogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, --COOR₆ or --CONR₇ R₈,

R₁ is hydrogen, halogen, C₁ -C₅ alkyl, C₂ -C₅ alkenyl or a radical--Y--R₅,

R₂ is hydrogen, halogen, C₁ -C₅ alkyl, C₂ -C₅ alkenyl, C₁ -C₄ haloalkyl,or a radical --Y--R₅, --COOR₆, --NO₂ or --CO--NR₇ --R₈,

R₃ and R₄, each independently of the other, are hydrogen, C₁ -C₄ alkyl,C₁ -C₄ alkoxy, C₁ -C₄ alkylthio, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkoxy, C₁-C₄ haloalkylthio, halogen, C₂ -C₅ alkoxyalkyl, --NR₉ R₁₀ or --O--CH₂--CH₂ --NR₉ R₁₀,

R₅ and R₆, each independently of the other, are C₁ -C₅ alkyl, C₂ -C₅alkenyl or C₂ -C₆ alkynyl, C₁ -C₅ haloalkyl, C₂ -C₅ haloalkenyl or C₂-C₆ alkoxyalkyl,

R₇ and R₈, each independently of the other, are hydrogen, C₁ -C₅ alkyl,C₂ -C₅ alkenyl or C₂ -C₆ alkynyl,

R₉ is hydrogen, methyl or ethyl,

R₁₀ is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, methoxymethyl,cyanomethyl, cyanoethyl, C₃ -C₅ alkenyl or C₃ -C₆ alkynyl, and

Y is oxygen, sulfur, a sulfinyl or sulfonyl bridge.

Herbicidally active ureas, triazines and pyrimidines are generally knownin the art. Arysulfamoyl-heterocyclyl-aminocarbamoyl compounds withherbicidal and plant growth-regulating action are described e.g. inNetherlands patent specification No. 121 788 or in European patentapplication No. 44 210.

In the above definitions, alkyl denotes straight-chain or branchedalkyl, e.g. methyl, ethyl, n-propyl, isopropyl, the four butyl isomers,n-amyl, isoamyl, 2-amyl, 3-amyl, n-hexyl or isohexyl, or the differentheptyl, octyl or nonyl isomers.

Alkoxy denotes methoxy, ethoxy, n-propoxy, isopropoxy and the fourbutoxy isomers, with methoxy, ethoxy or isopropoxy being preferred.

Alkylthio is e.g. methylthio, ethylthio, n-propylthio, isopropylthio andn-butylthio, with methylthio and ethylthio being preferred.

Alkenyl radicals are e.g. vinyl, allyl, isoprenyl, propen-1-yl,buten-1-yl, buten-2-yl, buten-3-yl, isobuten-1-yl, isobuten-2-yl,penten-1-yl, penten-2-yl, penten-3-yl and penten-4-yl, with vinyl, allyland penten-4-yl being preferred.

Halogen in the above definitions, as well as moiety of haloalkyl,haloalkoxy and haloalkylthio, is fluorine, chlorine and bromine, withfluorine and chlorine being preferred.

Alkynyl radicals in the above definitions are generally propargyl,butyn-2-yl, butyn-3-yl, as well as pentynyl or hexynyl isomers.Preferably, however, alkynyl is propargyl or butyn-2- or -3-yl.

Aromatic heterocyclic rings which may be a constituent of thesubstituent A are e.g.: furan, thiophene, pyrrole, pyrazole, triazole,pyridine, pyrimidine, pyridazine, triazine, thiazole, oxazole,thiadiazole or oxadiazole. Furan, thiophene and pyridine are preferred.These aromatic heterocyclic rings are most preferred when they arelinked in the 2-position to the ethynyl bridge.

The invention also comprises the salts which the compounds of formula Iare able to form with amines, alkali metal bases and alkaline earthmetal bases, or with quaternary ammonium bases.

Preferred salt-forming alkali metal hydroxides and alkaline earth metalhydroxides are the hydroxides of lithium, sodium, potassium, magnesiumor calcium, most preferably those of sodium or potassium.

Examples of suitable salt-forming amines are primary, secondary andtertiary aliphatic and aromatic amines such as methylamine, ethylamine,propylamine, isopropylamine, the four butylamine isomers, dimethylamine,diethylamine, diethanolamine, diisopropylamine, diisopropylamine,di-n-butylamine, pyrrolidine, piperidine, morpholine, trimethylamine,triethylamine, tripropylamine, quinuclidine, pyridine, quinoline andisoquinoline. Preferred amines are ethylamine, propylamine, diethylamineor triethylamine, with isopropylamine and diethanolamine being mostpreferred.

Examples of quaternary ammonium bases are, in general, the cations ofhaloammonium salts, e.g. the tetramethylammonium cation, thetrimethylbenzylammonium cation, the triethylbenzylammonium cation, thetetraethylammonium cation, the trimethylethylammonium cation, and alsothe ammonium cation.

Preferred compounds of the formula I are those in which

(a) Z is oxygen,

(b) R₃ and R₄ together contain not more than 4 carbon atoms, and

(c) m is 1.

Preferred compounds of group (c) are those in which the radical A is inthe 2- or 3-position to the sulfonyl group.

A particularly preferred group of compounds of the formula I comprisesthose compounds in which only one radical A is in the 2- or 3-positionto the sulfonyl group, Z is oxygen, and R₃ and R₄ together contain notmore than 4 carbon atoms.

Preferred compounds belonging to this group are those in which R₁ ishydrogen and R₂ is in the 5- or 6-position to the sulfonyl group. Amongthese compounds, those compounds are in turn preferred in which R₂ ishydrogen, halogen, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, nitro, C₁ -C₄alkyl, C₁ -C₄ haloalkyl or --COOR₆.

Further preferred compounds within this last mentioned group are thosecompounds in which R₂ is hydrogen, chlorine, fluorine, --COOR₆, nitro,methyl, trifluoromethyl, C₁ -C₄ haloalkoxy or C₁ -C₄ alkoxy, and each ofR₃ and R₄ is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ alkylthio,dialkylamino, C₁ -C₃ haloalkoxy, halogen or alkoxyalkyl, whilst R₃ andR₄ together contain not more than 1 to 4 carbon atoms.

Among the individually preferred subgroups of compounds of formula I,those groups always merit particular preference in which R is hydrogenor branched or unbranched C₁ -C₄ alkyl which is unsubstituted orsubstituted by halogen, hydroxyl, methoxy, methylthio, C₁ -C₄haloalkoxy, cyclopropyl, cyano or methoxycarbonyl, or is phenyl,pyridyl, thienyl or furyl.

A most particularly preferred subgroup comprises those compounds offormula I, wherein R₁ is hydrogen, R₂ is hydrogen, chlorine, fluorine,nitro, methyl, trifluoromethyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkyl or C₁-C₄ -alkoxycarbonyl which is in the 6-position, m is 1, and each of R₃and R₄ is C₁ -C₄ alkyl, C₁ -C₄ alkoxy, methylthio, C₁ -C₂ haloalkyl,halogen or alkoxyalkyl, whilst R₃ and R₄ together contain not more than4 carbon atoms, R is hydrogen or unbranched or branched C₁ -C₄ alkylwhich is unsubstituted or substituted by halogen, hydroxyl, methoxy,methylthio, C₁ -C₄ haloalkoxy, cyclopropyl, cyano or methoxycarbonyl, oris phenyl, pyridyl, thienyl or furyl.

Preferred individual compounds are:

N-[2-(propyn-1-yl)-phenylsulfonyl]-N'-(4,6-dimethoxypyrimidin-2-yl)urea,

N-[2-(propyn-1-yl)-phenylsulfonyl]-N'-(4-methoxy-6-methylpyrimidin-2-yl)urea,

N-[2-(propyn-1-yl)-phenylsulfonyl]-N'-(4,6-dimethylpyrimidin-2-yl)urea,

N-[2-(2-phenylethynyl)-phenylsulfonyl]-N'-(4,6-dimethoxypyrimidin-2-yl)urea

N-[2-(propyn-1-yl)-phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureaand

N-[2-(3-hydroxy-3'-methylbutyn-1'-yl)-phenylsulfonyl]-N'-(4,6-dimethoxypyrimidin-2-yl)urea.

The process for obtaining the compounds of formula I is carried out inan inert organic solvent.

In a first process, the compounds of the formula I are obtained byreacting a phenylsulfonamide of the formula II ##STR3## wherein A, R₁,R₂ and m are as defined for formula I, with a N-pyrimidinylcarbamate orN-triazinylcarbamate of the formula III ##STR4## wherein E, R₃, R₄ and Zare as defined for formula I, and R₁₁ is hydrogen, halogen, C₁ -C₄alkyl, C₁ -C₄ alkoxy, nitro, cyano or trifluoromethyl, in the presenceof a base.

In a second process, compounds of formula I are obtained by reacting aphenylsulfonylisocyanate or phenylsulfonylisothiocyanate of the formulaIV ##STR5## wherein A, R₁, R₂, m and Z are as defined for formula I,with an amine of the formula V R1 ? ##STR6## wherein E, R₃ and R₄ are asdefined for formula I, in the presence of a base.

In a further process, the compounds of formula I are obtained byreacting a sulfonamide of the formula II above with an isocyanate orisothiocyanate of the formula VI ##STR7## wherein E, R₃, R₄ and Z are asdefined for formula I, optionally in the presence of a base.

Finally, the compounds of formula I can also be obtained by reacting aN-phenylsulfonylcarbamate of the formula VII ##STR8## wherein A, R₁, R₂and m are as defined for formula I, and R₁₂ is hydrogen, halogen, C₁ -C₄alkyl, C₁ -C₄ alkoxy, nitro, cyano or trifluoromethyl, with an amine ofthe formula V above.

If desired, the ureas of formula I can be converted into salts withamines, alkali metal hydroxides or alkaline earth metal hydroxides, orwith quaternary ammonium bases. This conversion is carried out e.g. byreacting the compounds of formula I with the equimolar amount of a baseand removing the solvent by evaporation.

The starting materials of the formulae II, IV and VII are novel and canbe prepared by the following methods.

The novel sulfonamides of formula II used as intermediates are obtainedfrom the corresponding halophenylsulfonamides (IX) by reaction withacetylene compounds in accordance with the following reaction scheme A.Similar methods of obtaining ethynyl compounds are described in Europeanpatent application No. 41 476. ##STR9##

In scheme A, the symbols R, R₁ and R₂ are as defined for formula I, withthe proviso that R in formula XI is an aromatic radical. Hal ischlorine, but bromine and iodine are preferred. Alkyl is a C₁ -C₄ alkylradical.

Method α is a process which makes it possible, using metal catalysts, tobond halogenated radicals, as in formula IX or XI, to terminal acetylenegroups, as in formulae VIII, X and XIII, under mild reaction conditions,in the presence of an acid acceptor. Reactions of this kind aredescribed in the following publications: K. Sonogashire, Y. Tohda and N.Hagihara, Tetrahedron Lett., 50, 4467 (1975); L. Cassar, J. Organomet.Chem., 93, 253 (1975), and H. A. Dieck and F. R. Heck, J. Organomet.Chem., 93, 259 (1975).

This reaction conveniently takes place in organic solvents which areinert to the reactants. Suitable solvents of this kind are many proticand aprotic solvents, e.g. alkanols, ketones, ethers, hydrocarbons,halogenated hydrocarbons, aromatic solvents such as methanol, ethanol,isopropanol, cyclohexanone, acetone, methyl ethyl ketone, diethyl ether,dimethyl ether, tetrahydrofuran, dioxan, cyclohexane, pentane, hexane,heptane, octane, methylene chloride, chloroform, carbon tetrachloride,benzene, toluene or xylene, or also e.g. dimethylformamide,dimethylsulfoxide, acetonitrile or tertiary amines such astriethylamine.

As dehydrohalogenation occurs during the reaction, a base can be used asacid acceptor. Suitable bases are e.g. strong inorganic bases such asKOH or NaOH, and also organic bases, such as triethylamine,diethylamine, pyridine, alcoholates etc. The amount of base employed inthe reaction is from 1 to 5 equivalents. As metal catalysts it ispreferred to use palladium salts or complexes, in particular palladiumchloride (PdCl₂), palladium acetate (Pd(OCOCH₃)₂), or the palladiumdichlorobis(triphenylphosphine) complex PdCl₂ [P(C₆ H₅)₃ ]₂, usuallywith the addition of a copper(I) salt, especially of copper(I) iodide.The catalysts are employed by themselves or applied to a carrier, e.g.ground charcoal, alumina etc.

The reaction temperatures are generally in the range from 0° C. to 200°C., but are in the main between room temperature and the boiling pointof the reaction mixture. The reaction times are generally from 1/2 hourto 48 hours.

Method β makes it possible, in the presence of a strong base such asNaOH, KOH or an alcoholate, to liberate the acetylene from a tertiaryethynyl alcohol, as in formulae X, XII and XIV, which may be unterstoodas a protected terminal acetylene group, with removal of the ketoprotective group, as in formulae VIII and XIII. The ketones obtained asby-products can be removed from the reaction mixture by distillationduring the reaction. Reactions of this kind are described in GermanOffenlegungsschrift No. 2 905 507 and U.S. Pat. No. 4,128,588.

It is advantageous to conduct this reaction in an inert organic solventsuch as an alcohol, an ether, a ketone, a hydrocarbon, a halogenatedhydrocarbon, an aromatic solvent, or also in dimethylformamide,dimethylsulfoxide or acetonitrile. Examples of such solvents are:methanol, ethanol, isopropanol, dimethyl ether, diethyl ether,tetrahydrofuran, dioxan, acetone, methyl ethyl ketone, cyclohexanone,cyclohexane, benzene, toluene, xylene, methylene chloride, chloroform orcarbon tetrachloride.

The reaction temperature in this case too is also preferably in therange between room temperature and the boiling point of the solvent. Thereaction time is generally from 1/2 hour to 12 hours.

Method γ is a combination of methods α and β, except that the acetyleneto be reacted by method α is prepared in situ by treating a protectedacetylene of the formula X, XII and XIV with a strong base. The reactionconditions are identical with those of method α. However, the additionof a strong base such as NaOH, KOH or the alkali metal salt of analcohol, is mandatory.

In accordance with the process outlined above, the compounds of formulaII are obtained elither by reacting an ethynyl compound of the formulaVIII

    R--C.tbd.CH                                                (VIII)

with a halophenylsulfonamide of the formula IX ##STR10## in the presenceof an acid acceptor and a metal catalyst and, if desired, in an inertgas atmosphere, or by reacting an aromatic halide of the formula XI

    Hal--R'                                                    (XI)

under the same reaction conditions, with an ethynyl phenylsulfonamide ofthe formula XIII ##STR11## in which formulae above R₁ and R₂ are asdefined for formula I, R' is an aromatic radical and Hal is bromine oriodine.

In a further process, the compounds of formula II are obtained byreacting an aromatic halide of the formula XI

    Hal--R'                                                    (XI)

with a propargyl alcohol of the formula X ##STR12## in the presence ofan acid acceptor and a metal catalyst and, if desired, under an inertgas atmosphere, and reacting the resultant ethynyl compound of theformula XII ##STR13## with a halophenylsulfonamide of the formula IX##STR14## in the presence of a strong base and a metal catalyst, ifdesired under an inert gas atmosphere, or by reacting thehalophenylsulfonamide of the formula IX, under the above reactionconditions, first with the propargyl alcohol of the formula X, and thenreacting the ethynyl compound of the formula XIV ##STR15## under theabove conditions, with the aromatic halide of the formula XI, in whichformulae above R₁ and R₂ are as defined for formula I, Hal is bromine oriodine and alkyl is a C₁ -C₄ alkyl radical.

The compounds of formula II employed as intermediates are novel and havebeen specially developed for the synthesis of compounds of formula I.These intermediates constitute a further object of the invention.

The phenylsulfonylisocyanates of the formula IV can be obtained byreacting the phenylsulfonamides of the formula II with phosgene, in thepresence of butylisocyanate, in a chlorinated hydrocarbon as solvent, atreflux temperature. Similar reactions are described in "Newer Methods ofPreparative Organic Chemistry", Vol. VI, 223-241, Academic Press, NewYork and London.

The isothiocyanates of the formula IV are obtained by treating thephenylsulfonamides of formula II with carbon disulfide and potassiumhydroxide and by subsequent reaction of the dipotassium salt withphosgene. Such processes are described in Arch. Pharm. 299, 174 (1966).

The N-phenylsulfonylcarbamates of the formula VII are obtained byreacting the phenylsulfonamides of the formula II with diphenylcarbonate in the presence of a base. Similar processes are described inJapanese patent specification No. 61 169.

The starting materials of the formulae III, V and VI are known or theycan be prepared by known methods.

Isocyanates of the formula VI can be prepared by reacting amines of theformula V with oxalyl chloride in a chlorinated hydrocarbon as solvent.Amines of the formula V are known and some are commercially available,or they can be prepared by known methods, q.v. "The Chemistry ofHeterocyclic Compounds", Vol. XIV, Interscience Publishers, New York,London.

It is convenient to carry out these reactions for obtaining compounds offormula I in aprotic, inert organic solvents such as methylene chloride,tetrahydrofuran, acetonitrile, dioxan or toluene.

The reaction temperatures are preferably in the range from -20° to +120°C. The reactions are normally slightly exothermic and can be carried outat room temperature. To shorten the reaction time or also to initiatethe reaction it is expedient to heat the reaction mixture briefly toboiling point. The reaction times can also be shortened by addition of afew drops of a base or isocyanate as catalyst.

The final products can be isolated by concentrating the reaction mixtureand/or removing the solvent by evaporation, and by recrystallisation orby triturating the solid residue in a solvent in which it is poorlysoluble, such as an ether, an aromatic hydrocarbon or a chlorinatedhydrocarbon.

The compounds of formula I are stable compounds, and no protectivemeasures are required for handling them.

When used in low rates of application, the compounds of formula I havegood selective growth inhibiting and selective herbicidal propertieswhich make them most suitable for use in crops of useful plants,especially in cereals, cotton, soybeans, maize and rice. In some casesdamage is also caused to weeds which have only been controlled up to nowwith total herbicides.

The mode of action of some of these compounds is unusual. Many aretranslocatable, i.e. they are absorbed by the plant and transported toother parts of it where they then exert their action. Thus, for example,it is possible to damage perennial weeds to the roots by surfacetreatment. Compared with other herbicides and growth regulators, thenovel compounds of the formula I are effective even when used in verylow rates of application.

The compounds of formula I have pronounced growth-regulating, especiallygrowth-inhibiting, properties. The growth of both monocots and dicots isinhibited. Thus, for example, the compounds of formula I selectivelyinhibit the growth of leguminosae which are frequently planted as covercrops in tropical regions, so that, while soil erosion betweencultivated plants is prevented, the cover crops cannot compete with thecultivated plants.

Further, the compounds of formula I are suitable for preventing storedpotatoes from seeding. During winter storage, potatoes often developsprouts which result in shrinkage, weight loss, and rot.

At higher rates of application, all tested plants are so severelydamaged in their development that they die.

The invention also relates to herbicidal and growth-regulatingcompositions which contain a novel compound of the formula I, and alsoto methods of controlling weeds pre- and postemergence and of inhibitingthe growth of monocots and dicots, especially grasses, tropical covercrops and tobacco plant suckers.

The compounds of the formula I are used in unmodified form, orpreferably, together with the adjuvants conventionally employed in theart of formulation, and are therefore, formulated in known manner toemulsifiable concentrates, coatable pastes, directly sprayable ordilutable solutions, dilute emulsions, wettable powders, solublepowders, dusts, granulates, and also encapsulations in e.g. polymersubstances. As with the nature of the compositions, the methods ofapplication, such as spraying, atomising, dusting, scattering orpouring, are chosen in accordance with the intended objectives and theprevailing circumstances.

The formulations, i.e. the compositions containing the compound (activeingredient) of the formula I and, where appropriate, a solid or liquidadjuvant, are prepared in known manner, e.g. by homogeneously mixingand/or grinding the active ingredients with extenders, e.g. solvents,solid carriers and, where appropriate, surface-active compounds(surfactants).

Suitable solvents are: aromatic hydrocarbons, preferably the fractionscontaining 8 to 12 carbon atoms, e.g. xylene mixtures or substitutednaphthalenes, phthalates such as dibutyl phthalate or dioctyl phthalate,aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols andglycols and their ethers and esters, such as ethanol, ethylene glycolmonomethyl or monoethyl ether, ketones such as cyclohexanone, stronglypolar solvents such as N-methyl-2-pyrrolidone, dimethylsulfoxide ordimethylformamide, as well as epoxidised vegetable oils such asepoxidised coconut oil or soybean oil; or water.

The solid carriers used e.g. for dusts and dispersible powders, arenormally natural mineral fillers such as calcite, talcum, kaolin,montmorillonite or attapulgite. In order to improve the physicalproperties it is also possible to add highly dispersed silicic acid orhighly dispersed absorbent polymers. Suitable granulated adsorptivecarriers are porous types, for example pumice, broken brick, sepioliteor bentonite; and suitable nonsorbent carriers are materials such ascalcite or sand. In addition, a great number of pregranulated materialsof inorganic or organic nature can be used, e.g. especially dolomite orpulverised plant residues.

Depending on the nature of the compound of the formula I to beformulated, suitable surface-active compounds are nonionic, cationicand/or anionic surfactants having goot emulsifying, dispersing andwetting properties. The term "surfactants" will also be understood ascomprising mixtures of surfactants.

Suitable anionic surfactants can be both water-soluble soaps andwater-soluble synthetic surface-active compounds.

Suitable soaps are the alkali metal salts, alkaline earth metal salts orunsubstituted or substituted ammonium salts of higher fatty acids (C₁₀-C₂₂), e.g. the sodium or potassium salts of oleic or stearic acid, orof natural fatty acid mixtures which can be obtained e.g. from coconutoil or tallow oil. Mention may also be made of fatty acid methyltaurinsalts.

More frequently, however, so-called synthetic surfactants are used,especially fatty sulfonates, fatty sulfates, sulfonated benzimidazolederivatives or alkylarylsulfonates.

The fatty sulfonates or sulfates are usually in the form of alkali metalsalts, alkaline earth metal salts or unsubstituted or substitutedammonium salts and contain a C₈ -C₂₂ alkyl radical which also includesthe alkyl moiety of acyl radicals, e.g. the sodium or calcium salt oflignosulfonic acid, of dodecylsulfate or of a mixture of fatty alcoholsulfates obtained from natural fatty acids. These compounds alsocomprise the salts of sulfuric acid esters and sulfonic acids of fattyalcohol/ethylene oxide adducts. The sulfonated benzimidazole derivativespreferably contain 2 sulfonic acid groups and one fatty acid radicalcontaining 8 to 22 carbon atoms. Examples of alkylarylsulfonates are thesodium, calcium or triethylanolamine salts of naphthalenesulfonicacid/formaldehyde condensation product. Also suitable are correspondingphosphates, e.g. salts of the phosphoric acid ester of an adduct ofp-nonylphenol with 4 to 14 moles of ethylene oxide, or phospholipides.

Non-ionic surfactants are preferably polyglycol ether derivatives ofaliphatic or cycloaliphatic alcohols, or saturated or unsaturated fattyacids and alkylphenols, said derivatives containing 3 to 30 glycol ethergroups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moietyand 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.

Further suitable non-ionic surfactants are the water-soluble adducts ofpolyethylene oxide with polypropylene glycol, ethylenediamine propyleneglycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms inthe alkyl chain, which adducts contain 20 to 250 ethylene glycol ethergroups and 10 to 100 propylene glycol ether groups. These compoundsusually contain 1 to 5 ethylene glycol units per propylene glycol unit.

Representative examples of non-ionic surfactants arenonylphenolpolyethoxyethanols, castor oil polyglycol ethers,polypropylene/polyethylene oxide adducts,tributylphenoxypolyethoxyethanol, polyethylene glycol andoctylphenoxyethoxyethanol. Fatty acid esters of polyoxyethylene sorbitanand polyoxyethylene sorbitan trioleate are also suitable non-ionicsurfactants.

Cationic surfactants are preferably quaternary ammonium salts whichcontain, as N-substituent, at least one C₈ -C₂₂ alkyl radical and, asfurther substituents, lower unsubstituted or halogenated alkyl, benzylor lower hydroxyalkyl radicals. The salts are preferably in the form ofhalides, methylsulfates or ethylsulfates, e.g. stearyltrimethylammoniumchloride or benzyldi(2-chloroethyl)ethylammonium bromide.

The surfactants customarily employed in the art of formulation aredescribed e.g. in "McCutcheon's Detergents and Emulsifiers Annual", MCPublishing Corp. Ridgewood, N.J., 1979, and Sisley and Wood,"Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc.New York, 1964.

The pesticidal compositions usually contain 0.1 to 95%, preferably 0.1to 80%, of a compound of the formula I, 1 to 99.9%, of a solid or liquidadjuvant, and 0 to 25%, preferably 0.1 to 25%, of a surfactant.

Preferred formulations are composed in particular of the followingconstituents (%=percentage by weight):

    ______________________________________                                        Emulsifiable concentrates                                                     active ingredient:                                                                           10 to 20%, preferably  5 to 10%                                surfactant:    5 to 30%,  preferably 10 to 20%                                liquid carrier:                                                                              20 to 94%, preferably 70 to 85%                                Dusts                                                                         active ingredient:                                                                           0.1 to 10%,                                                                              preferably  0.1 to 1%                               solid carrier: 99.9 to 90%,                                                                             preferably 99.9 to 99%                              Suspension concentrates                                                       active ingredient:                                                                           5 to 75%,  preferably 10 to 50%                                water:         94 to 25%, preferably 90 to 30%                                surfactant:    1 to 40%,  preferably  2 to 30%                                Wettable powders                                                              active ingredient:                                                                           0.5 to 90%,                                                                              preferably 10 to 80%                                surfactant:    0.5 to 20%,                                                                              preferably  1 to 15%                                solid carrier: 5 to 95%,  preferably 15 to 90%                                Granulates                                                                    active ingredient:                                                                           0.5 to 30%,                                                                              preferably  3 to 15%                                solid carrier: 99.5 to 70%,                                                                             preferably 97 to 85%.                               ______________________________________                                    

Whereas commerical products will be preferably formulated asconcentrates, the end user will normally employ dilute formulations. Theformulations can be diluted to a concentration as low as 0.001%. Therates of application are normally from 0.01 to 10 kg a.i./ha, preferablyfrom 0.025 to 5 kg a.i./ha.

The compositions may also contain further ingredients, such asstabilisers, antifoams, viscosity regulators, binders, tackifiers aswell as fertilisers or other active ingredients in order to obtainspecial effects.

PREPARATORY EXAMPLES Example 1 ##STR16##N-[2-(propyn-1-yl)phenylsulfonyl]-N'-(4,6-dimethoxypyrimidin-2-yl)urea(compound 5.1)

(a) 2-(propyn-1-yl)phenylsulfonamide:

To a solution of 28.3 g (0.1 mole) of 2-iodophenylsulfonamide in 350 mlof dimethylformamide and 100 ml of triethylamine are added 1.0 g ofpalladium dichloro-bis(triphenylphosphite) complex, PdCl₂ [P(C₆ H₅)₃ ]₂,and 0.5 g of copper(I) iodide (CuI). Gaseous propine is then introducedinto this solution until the starting material is completely reacted.The reaction mixture is filtered and the residue is concentrated invacuo and then taken up in water. The precipitate is isolated and dried.Recrystallisation from ethyl acetate/hexane yields 15.6 g (80%) of2-(propyn-1-yl)phenylsulfonamide with a melting point of 147°-149° C.

(b)N-[2-(propyn-1-yl)phenylsulfonyl]-N'-4,6-dimethoxypyrimidin-2-yl)urea:

To a solution of 1.95 g (0.01 mole) of 2-(propyn-1-yl)phenylsulfonamideand 1.7 g of 1,8-diazabicyclo[5.4.0]-undec-7-ene in 33 ml of absolutedioxan are added, in portions, 2.75 g (1.01 mole) of4,6-dimethoxy-2-phenoxycarbonylaminopyridine at 20°-25° C. over 30minutes. The reaction mixture is subsequently stirred for 4 hours at20°-25° C. and then taken up in a mixture of 66 ml of ice-water, 10 mlof 2N hydrochloric acid and 150 ml of ethyl acetate. The organic phaseis separated and the aqueous phase is extracted with 66 ml of ethylacetate. The combined organic extracts are washed with water and asaturated solution of sodium chloride, dried over magnesium sulfate andconcentrated. The crystalline residue is washed with diethyl ether,affording 2.4 g (74%) ofN-[2-(propyn-1-yl)phenylsulfonyl]-N'-4,6-dimethoxypyrimidin-2-yl)ureawith a melting point of 193°-194° C.

The intermediates and final products listed in the subsequent tables areobtained in corresponding manner.

                  TABLE 1                                                         ______________________________________                                         ##STR17##                                                                    No.    R             R.sub.2    R.sub.1                                                                           m.p. [°C.]                         ______________________________________                                        1.1    CH.sub.3      H          H   147-149                                   1.2    H             H          H                                             1.3    C(CH.sub.3).sub.2OH                                                                         H          H   200-201                                   1.4    C.sub.6 H.sub.5                                                                             H          H   85-88                                     1.5    4-ClC.sub.6 H.sub.4                                                                         H          H                                             1.6    2-thienyl     H          H                                             1.7    2-furyl       H          H                                             1.8    2-pyridyl     H          H                                             1.9    CH.sub.3      5-F        H                                             1.10   H             5-F        H                                             1.11   C(CH.sub.3).sub.2OH                                                                         5-F        H                                             1.12   C.sub.6 H.sub.5                                                                             5-F        H                                             1.13   2-thienyl     5-F        H                                             1.14   2-furyl       5-F        H                                             1.15   CH.sub.3      6-Cl       H                                             1.16   CH.sub.3      6-COOCH.sub.3                                                                            H                                             1.17   CH.sub.3      6-OCH.sub.3                                                                              H                                             1.18   CH.sub.3      6-OCHF.sub.2                                                                             H                                             1.19   CH.sub.3      6-CF.sub.3 H                                             1.20   CH.sub.3      6-CH.sub.3 H                                             ______________________________________                                    

                  TABLE 2                                                         ______________________________________                                         ##STR18##                                                                    No.    R             R.sub.2    R.sub.1                                                                           m.p. [°C.]                         ______________________________________                                        2.1    CH.sub.3      6-Cl       H                                             2.2    H             6-Cl       H                                             2.3    C(CH.sub.3).sub.2OH                                                                         6-Cl       H                                             2.4    C.sub.6 H.sub.5                                                                             6-Cl       H                                             2.5    CH.sub.3      6-F        H                                             2.6    H             6-F        H                                             2.7    C(CH.sub.3).sub.2OH                                                                         6-F        H                                             2.8    C.sub.6 H.sub.5                                                                             6-F        H                                             2.9    CH.sub.3      H          H                                             2.10   H             H          H                                             2.11   CH.sub.3      6-COOCH.sub.3                                                                            H                                             2.12   CH.sub.3      6-CF.sub.3 H                                             2.13   CH.sub.3      6-OCH.sub.3                                                                              H                                             2.14   CH.sub.3      6-OCHF.sub.2                                                                             H                                             2.15   CH.sub.3      6-CH.sub.3 H                                             ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                         ##STR19##                                                                    No.     R              R.sub.2 R.sub.1                                                                            m.p. [°C.]                         ______________________________________                                        3.1     CH.sub.3       H       H                                              3.2     H              H       H                                              3.3     C(CH.sub.3).sub.2OH                                                                          H       H                                              3.4     C.sub.6 H.sub.5                                                                              H       H                                              3.5     4-ClC.sub.6 H.sub.4                                                                          H       H                                              3.6     2-thienyl      H       H                                              3.7     2-furyl        H       H                                              3.8     2-pyridyl      H       H                                              3.9     CH.sub.3       5-F     H                                              3.10    H              5-F     H                                              3.11    C(CH.sub.3).sub.2OH                                                                          5-F     H                                              3.12    C.sub.6 H.sub.5                                                                              5-F     H                                              3.13    2-thienyl      5-F     H                                              3.14    2-furyl        5-F     H                                              ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                         ##STR20##                                                                    No.     R             R.sub.2 R.sub.1                                                                           m.p. [°C.]                           ______________________________________                                        4.1     CH.sub.3      6-Cl    H                                               4.2     H             6-Cl    H                                               4.3     C(CH.sub.3).sub.2OH                                                                         6-Cl    H                                               4.4     C.sub.6 H.sub.5                                                                             6-Cl    H                                               4.5     CH.sub.3      6-F     H                                               4.6     H             6-F     H                                               4.7     C(CH.sub.3).sub.2OH                                                                         6-F     H                                               4.8     C.sub.6 H.sub.5                                                                             6-F     H                                               ______________________________________                                    

                                      TABLE 5                                     __________________________________________________________________________     ##STR21##                                                                    No.                                                                              R        R.sub.2                                                                             R.sub.1                                                                         R.sub.3                                                                             R.sub.4     E  Z m.p. [°C.]                  __________________________________________________________________________    5.1                                                                              CH.sub.3 H     H OCH.sub.3                                                                           OCH.sub.3   CH O 193-194                            5.2                                                                              CH.sub.3 H     H CH.sub.3                                                                            CH.sub.3    CH O 187-189                            5.3                                                                              CH.sub.3 H     H CH.sub.3                                                                            OCH.sub.3   CH O 193                                                                           (decomp.)                          5.4                                                                              CH.sub.3 H     H OCH.sub.3                                                                           OCH.sub.3   N  O                                    5.5                                                                              CH.sub.3 H     H CH.sub.3                                                                            OCH.sub.3   N  O 168-170                            5.6                                                                              CH.sub.3 H     H OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                         N  O                                    5.7                                                                              CH.sub.3 H     H CH.sub.3                                                                            OCHF.sub.2  CH O                                    5.8                                                                              CH.sub.3 H     H OCH.sub.3                                                                           OCH.sub.2CF.sub.3                                                                         N  O                                    5.9                                                                              H        H     H OCH.sub.3                                                                           OCH.sub.3   CH O                                    5.10                                                                             H        H     H CH.sub.3                                                                            CH.sub.3    CH O                                    5.11                                                                             H        H     H CH.sub.3                                                                            OCH.sub.3   CH O                                    5.12                                                                             H        H     H OCH.sub.3                                                                           OCH.sub.3   N  O                                    5.13                                                                             H        H     H CH.sub.3                                                                            OCH.sub.3   N  O                                    5.14                                                                             H        H     H OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                         N  O                                    5.15                                                                             H        H     H CH.sub.3                                                                            OCHF.sub.2  CH O                                    5.16                                                                             H        H     H OCH.sub.3                                                                           OCH.sub.2CF.sub.3                                                                         N  O                                    5.17                                                                             C.sub.6 H.sub.5                                                                        H     H OCH.sub.3                                                                           OCH.sub.3   CH O 166-169                            5.18                                                                             C.sub.6 H.sub.5                                                                        H     H CH.sub.3                                                                            CH.sub.3    CH O                                    5.19                                                                             C.sub.6 H.sub.5                                                                        H     H CH.sub.3                                                                            OCH.sub.3   CH O                                    5.20                                                                             C.sub.6 H.sub.5                                                                        H     H OCH.sub.3                                                                           OCH.sub.3   N  O                                    5.21                                                                             C.sub.6 H.sub.5                                                                        H     H CH.sub.3                                                                            OCH.sub.3   N  O                                    5.22                                                                             C.sub.6 H.sub.5                                                                        H     H OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                         N  O                                    5.23                                                                             C.sub.6 H.sub.5                                                                        H     H CH.sub.3                                                                            OCHF.sub.2  CH O                                    5.24                                                                             C.sub.6 H.sub.5                                                                        H     H OCH.sub.3                                                                           OCH.sub.2CF.sub.3                                                                         N  O                                    5.25                                                                             4-ClC.sub.6 H.sub.4                                                                    H     H OCH.sub.3                                                                           OCH.sub.3   CH O                                    5.26                                                                             4-ClC.sub.6 H.sub.4                                                                    H     H CH.sub.3                                                                            CH.sub.3    CH O                                    5.27                                                                             4-ClC.sub.6 H.sub.4                                                                    H     H CH.sub.3                                                                            OCH.sub.3   CH O                                    5.28                                                                             4-ClC.sub.6 H.sub.4                                                                    H     H OCH.sub.3                                                                           OCH.sub.3   N  O                                    5.29                                                                             4-ClC.sub.6 H.sub.4                                                                    H     H CH.sub.3                                                                            OCH.sub.3   N  O                                    5.30                                                                             4-ClC.sub.6 H.sub.4                                                                    H     H OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                         N  O                                    5.31                                                                             4-ClC.sub.6 H.sub.4                                                                    H     H CH.sub.3                                                                            OCHF.sub.2  CH O                                    5.32                                                                             4-ClC.sub.6 H.sub.4                                                                    H     H OCH.sub.3                                                                           OCH.sub.2CF.sub.3                                                                         N  O                                    5.33                                                                             C(CH.sub.3).sub.2OH                                                                    H     H OCH.sub.3                                                                           OCH.sub.3   CH O 150                                5.34                                                                             C(CH.sub.3).sub.2OH                                                                    H     H CH.sub.3                                                                            CH.sub.3    CH O                                    5.34                                                                             C(CH.sub.3).sub.2OH                                                                    H     H CH.sub.3                                                                            OCH.sub.3   CH O                                    5.36                                                                             C(CH.sub.3).sub.2OH                                                                    H     H OCH.sub.3                                                                           OCH.sub.3   N  O                                    5.37                                                                             C(CH.sub.3).sub.2OH                                                                    H     H CH.sub.3                                                                            OCH.sub.3   N  O                                    5.38                                                                             C(CH.sub.3).sub.2OH                                                                    H     H OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                         N  O                                    5.39                                                                             C(CH.sub.3).sub.2OH                                                                    H     H CH.sub.3                                                                            OCHF.sub.2  CH O                                    5.40                                                                             C(CH.sub.3).sub.2OH                                                                    H     H OCH.sub.3                                                                           OCH.sub.2CF.sub.3                                                                         N  O                                    5.41                                                                             C.sub.2 H.sub.5                                                                        H     H OCH.sub.3                                                                           OCH.sub.3   CH O                                    5.42                                                                             C.sub.2 H.sub.5                                                                        H     H CH.sub.3                                                                            CH.sub.3    CH O                                    5.43                                                                             C.sub.2 H.sub.5                                                                        H     H CH.sub.3                                                                            OCH.sub.3   CH O                                    5.44                                                                             C.sub.2 H.sub.5                                                                        H     H OCH.sub.3                                                                           OCH.sub.3   N  O                                    5.45                                                                             C.sub.2 H.sub.5                                                                        H     H CH.sub.3                                                                            OCH.sub.3   N  O                                    5.46                                                                             C.sub.2 H.sub.5                                                                        H     H OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                         N  O                                    5.47                                                                             C.sub.2 H.sub.5                                                                        H     H CH.sub.3                                                                            OCHF.sub.2  CH O                                    5.48                                                                             C.sub.2 H.sub.5                                                                        H     H OCH.sub.3                                                                           OCH.sub.2CF.sub.3                                                                         N  O                                    5.49                                                                             2-thienyl                                                                              H     H OCH.sub.3                                                                           OCH.sub.3   CH O                                    5.50                                                                             2-thienyl                                                                              H     H CH.sub.3                                                                            CH.sub.3    CH O                                    5.51                                                                             2-thienyl                                                                              H     H CH.sub.3                                                                            OCH.sub.3   CH O                                    5.52                                                                             2-thienyl                                                                              H     H OCH.sub.3                                                                           OCH.sub.3   N  O                                    5.53                                                                             2-thienyl                                                                              H     H CH.sub.3                                                                            OCH.sub.3   N  O                                    5.54                                                                             2-thienyl                                                                              H     H OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                         N  O                                    5.55                                                                             2-thienyl                                                                              H     H CH.sub.3                                                                            OCHF.sub.2  CH O                                    5.56                                                                             2-thienyl                                                                              H     H OCH.sub.3                                                                           OCH.sub.2CF.sub.3                                                                         N  O                                    5.57                                                                             2-pyridyl                                                                              H     H OCH.sub.3                                                                           OCH.sub.3   CH O                                    5.58                                                                             2-pyridyl                                                                              H     H CH.sub.3                                                                            CH.sub.3    CH O                                    5.59                                                                             2-pyridyl                                                                              H     H CH.sub.3                                                                            OCH.sub.3   CH O                                    5.60                                                                             2-pyridyl                                                                              H     H OCH.sub.3                                                                           OCH.sub.3   N  O                                    5.61                                                                             2-pyridyl                                                                              H     H CH.sub.3                                                                            OCH.sub.3   N  O                                    5.62                                                                             2-pyridyl                                                                              H     H OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                         N  O                                    5.63                                                                             2-pyridyl                                                                              H     H CH.sub.3                                                                            OCHF.sub.2  CH O                                    5.64                                                                             2-pyridyl                                                                              H     H OCH.sub.3                                                                           OCH.sub.2CF.sub.3                                                                         N  O                                    5.65                                                                             CH.sub.3 H     H Cl    OCH.sub.3   CH O                                    5.66                                                                             CH.sub.3 H     H OCH.sub. 3                                                                          OCHF.sub.2  CH O                                    5.67                                                                             CH.sub.3 H     H Cl    OCHF.sub.2  CH O                                    5.68                                                                             CH.sub.3 H     H OCHF.sub.2                                                                          OCHF.sub.2  CH O                                    5.69                                                                             CH.sub.3 H     H OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                         CH O                                    5.70                                                                             CH.sub.3 H     H OCH.sub.3                                                                           CF.sub.3    CH O                                    5.71                                                                             CH.sub.3 H     H OCH.sub.3                                                                           CH.sub.2 F  CH O                                    5.72                                                                             CH.sub.3 H     H OCH.sub.3                                                                           SCH.sub.3   CH O                                    5.73                                                                             CH.sub.3 H     H OCH.sub.3                                                                           SCHF.sub.2  CH O                                    5.74                                                                             CH.sub.3 H     H OCHF.sub.2                                                                          N(CH.sub.3).sub.2                                                                         CH O                                    5.75                                                                             CH.sub.3 H     H OCH.sub.3                                                                           NHCH.sub.3  N  O                                    5.76                                                                             CH.sub.2 H     H OCH.sub.3                                                                           C.sub.2 H.sub.5                                                                           N  O                                    5.77                                                                             CH.sub.3 H     H OCH.sub.3                                                                           OCH.sub.2CH.sub.2 Cl                                                                      N  O                                    5.78                                                                             CH.sub.3 H     H CH.sub.3                                                                            O(CH.sub.2).sub.2N(CH.sub.3).sub.2                                                        N  O                                    5.79                                                                             CH.sub.3 H     H CH.sub.3                                                                            O(CH.sub.2).sub.2N(C.sub.2 H.sub.5).sub.2                                                 N  O                                    5.80                                                                             CH.sub.3 H     H OCH.sub.3                                                                           O(CH.sub.2).sub.2N(CH.sub.3).sub.2                                                        N  O                                    5.81                                                                             CH.sub.3 H     H OCH.sub.3                                                                           O(CH.sub.2).sub.2N(C.sub.2 H.sub.5).sub.2                                                 N  O                                    5.82                                                                             CH.sub.3 H     H CH.sub.3                                                                            O(CH.sub.2).sub.2N(CH.sub.3).sub.2                                                        CH O                                    5.83                                                                             CH.sub.3 H     H CH.sub.3                                                                            O(CH.sub.2).sub.2N(C.sub.2 H.sub.5).sub.2                                                 CH O                                    5.84                                                                             CH.sub.3 H     H OCH.sub.3                                                                           O(CH.sub.2).sub.2N(CH.sub.3).sub.2                                                        CH O                                    5.85                                                                             CH.sub.3 H     H OCH.sub.3                                                                           O(CH.sub.2).sub.2N(C.sub.2 H.sub.5).sub.2                                                 CH O                                    5.86                                                                             H        H     H Cl    OCH.sub.3   CH O                                    5.87                                                                             H        H     H OCH.sub.3                                                                           OCHF.sub.2  CH O                                    5.88                                                                             H        H     H Cl    OCHF.sub.2  CH O                                    5.89                                                                             H        H     H OCHF.sub.2                                                                          OCHF.sub.2  CH O                                    5.90                                                                             H        H     H OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                         CH O                                    5.91                                                                             H        H     H OCH.sub.3                                                                           CF.sub.3    CH O                                    5.92                                                                             H        H     H OCH.sub.3                                                                           CH.sub.2 F  CH O                                    5.93                                                                             H        H     H OCH.sub.3                                                                           SCH.sub.3   CH O                                    5.94                                                                             H        H     H OCH.sub.3                                                                           SCHF.sub.2  CH O                                    5.95                                                                             H        H     H OCHF.sub. 2                                                                         N(CH.sub.3).sub.2                                                                         CH O                                    5.96                                                                             H        H     H OCH.sub.3                                                                           NHCH.sub.3  N  O                                    5.97                                                                             H        H     H OCH.sub.3                                                                           C.sub.2 H.sub.5                                                                           N  O                                    5.98                                                                             H        H     H OCH.sub.3                                                                           OCH.sub.2CH.sub.2 Cl                                                                      N  O                                    5.99                                                                             H        H     H CH.sub.3                                                                            OCH.sub.3   N  S                                    5.100                                                                            H        H     H CH.sub.3                                                                            OCH.sub.3   CH S                                    5.101                                                                            H        H     H CH.sub.3                                                                            CH.sub.3    CH S                                    5.102                                                                            H        H     H OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                         N  S                                    5.103                                                                            H        H     H OCH.sub.3                                                                           OCH.sub.3   N  S                                    5.104                                                                            CH.sub.3 5-F   H OCH.sub.3                                                                           OCH.sub.3   CH O                                    5.105                                                                            CH.sub.3 5-F   H CH.sub.3                                                                            CH.sub.3    CH O                                    5.106                                                                            CH.sub.3 5-F   H CH.sub.3                                                                            OCHF.sub.2  CH O                                    5.107                                                                            CH.sub.3 5-F   H CH.sub.3                                                                            OCH.sub.3   N  O                                    5.108                                                                            CH.sub.3 5-F   H OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                         N  O                                    5.109                                                                            H        5-F   H OCH.sub.3                                                                           OCH.sub.3   CH O                                    5.110                                                                            H        5-F   H CH.sub.3                                                                            CH.sub.3    CH O                                    5.111                                                                            H        5-F   H CH.sub.3                                                                            OCHF.sub.2  CH O                                    5.112                                                                            H        5-F   H CH.sub.3                                                                            OCH.sub.3   N  O                                    5.113                                                                            H        5-F   H OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                         N  O                                    5.114                                                                            H        5-F   H OCH.sub.3                                                                           CH.sub.3    CH O                                    5.115                                                                            C(CH.sub.3).sub.2OH                                                                    5-F   H OCH.sub.3                                                                           OCH.sub.3   CH O                                    5.116                                                                            C(CH.sub.3).sub.2OH                                                                    5-F   H OCH.sub.3                                                                           CH          CH O                                    5.117                                                                            C(CH.sub.3).sub.2OH                                                                    5-F   H CH.sub.3                                                                            CH.sub.3    CH O                                    5.118                                                                            C(CH.sub.3).sub.2OH                                                                    5-F   H CH.sub.3                                                                            OCHF.sub.2  CH O                                    5.119                                                                            C(CH.sub.3).sub.2OH                                                                    5-F   H CH.sub.3                                                                            OCH.sub.3   N  O                                    5.120                                                                            C(CH.sub.3).sub.3OH                                                                    5-F   H OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                         N  O                                    5.121                                                                            C(CH.sub.3).sub.2OH                                                                    5-F   H OCH.sub.3                                                                           OCH.sub.3   N  O                                    5.122                                                                            C.sub.2 H.sub.5                                                                        5-F   H OCH.sub.3                                                                           OCH.sub.3   CH O                                    5.123                                                                            C.sub.2 H.sub.5                                                                        5-F   H CH.sub.3                                                                            OCH.sub.3   N  O                                    5.124                                                                            C.sub.6 H.sub.6                                                                        5-F   H OCH.sub.3                                                                           OCH.sub.3   N  O                                    5.125                                                                            C.sub.6 H.sub.5                                                                        5-F   H OCH.sub.3                                                                           N(CH.sub.3).sub.2                                                                         N  O                                    5.126                                                                            2-thienyl                                                                              5-F   H OCH.sub.3                                                                           OCH.sub.3   CH O                                    5.127                                                                            2-thienyl                                                                              5-F   H OCH.sub.3                                                                           CH.sub.3    N  O                                    5.128                                                                            2-furyl  5-F   H OCH.sub.3                                                                           OCH.sub.3   CH O                                    5.129                                                                            2-furyl  5-F   H CH.sub.3                                                                            OCH.sub.3   N  O                                    5.130                                                                            CH.sub.3 6-Cl  H OCH.sub.3                                                                           OCH.sub.3   CH O                                    5.131                                                                            CH.sub.3 6-Cl  H CH.sub.3                                                                            CH.sub.3    CH O                                    5.132                                                                            CH.sub.3 6-Cl  H CH.sub.3                                                                            OCH.sub.3   CH O                                    5.133                                                                            CH.sub.3 6-Cl  H CH.sub.3                                                                            OCHF.sub.2  CH O                                    5.134                                                                            CH.sub.3 6-Cl  H OCH.sub.3                                                                           OCH.sub.3   N  O                                    5.135                                                                            CH.sub.3 6-Cl  H CH.sub.3                                                                            OCH.sub.3   N  O                                    5.136                                                                            CH.sub.3 6-COOCH.sub.3                                                                       H CH.sub.3                                                                            OCH.sub.3   N  O                                    5.137                                                                            CH.sub.3 6-COOCH.sub.3                                                                       H CH.sub.3                                                                            OCH.sub.3   CH O                                    5.138                                                                            CH.sub.3 6-OCH.sub.3                                                                         H CH.sub.3                                                                            OCH.sub.3   N  O                                    5.139                                                                            CH.sub.3 6-OCH.sub.3                                                                         H CH.sub.3                                                                            OCH.sub.3   CH O                                    5.140                                                                            CH.sub.3 6-OCHF.sub.2                                                                        H CH.sub.3                                                                            OCH.sub.3   N  O                                    5.141                                                                            CH.sub.3 6-OCHF.sub.2                                                                        H CH.sub.3                                                                            OCH.sub.3   CH O                                    5.142                                                                            CH.sub.3 6-CF.sub.3                                                                          H CH.sub.3                                                                            OCH.sub.3   N  O                                    5.143                                                                            CH.sub.3 6-CF.sub.3                                                                          H CH.sub.3                                                                            OCH.sub.3   CH O                                    5.144                                                                            H        6-Cl  H CH.sub.3                                                                            OCH.sub.3   N  O                                    __________________________________________________________________________

                                      TABLE 6                                     __________________________________________________________________________     ##STR22##                                                                    No.                                                                              R        R.sub.2                                                                             R.sub.1                                                                         R.sub.3                                                                           R.sub.4                                                                             E  Z m.p. [°C.]                          __________________________________________________________________________    6.1                                                                              CH.sub.3 6-Cl  H CH.sub.3                                                                          OCHF.sub.2                                                                          CH O                                            6.2                                                                              CH.sub.3 6-Cl  H CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                            6.3                                                                              CH.sub.3 6-Cl  H OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                            6.4                                                                              H        6-Cl  H CH.sub.3                                                                          OCHF.sub.2                                                                          CH O                                            6.5                                                                              H        6-Cl  H CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                            6.6                                                                              H        6-Cl  H OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                            6.7                                                                              C(CH.sub.3).sub. 2OH                                                                   6-Cl  H OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                            6.8                                                                              C.sub.6 H.sub.5                                                                        6-Cl  H OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                            6.9                                                                              CH.sub.3 6-F   H OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                            6.10                                                                             CH.sub.3 6-F   H CH.sub.3                                                                          CH.sub.3                                                                            CH O                                            6.11                                                                             CH.sub.3 6-F   H CH.sub.3                                                                          OCHF.sub.2                                                                          CH O                                            6.12                                                                             CH.sub.3 6-F   H CH.sub.3                                                                          CH.sub.3                                                                            N  O                                            6.13                                                                             CH.sub.3 6-F   H OCH.sub.3                                                                         N(CH.sub.3).sub.2                                                                   N  O                                            6.14                                                                             H        6-F   H OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                            6.15                                                                             H        6-F   H CH.sub.3                                                                          CH.sub.3                                                                            CH O                                            6.16                                                                             H        6-F   H CH.sub.3                                                                          OCHF.sub.2                                                                          CH O                                            6.17                                                                             H        6-F   H CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                            6.18                                                                             H        6-F   H OCH.sub.3                                                                         N(CH.sub.3).sub.2                                                                   N  O                                            6.19                                                                             H        6-F   H OCH.sub.3                                                                         CH.sub.3                                                                            CH O                                            6.20                                                                             C(CH.sub.3).sub.2OH                                                                    6-F   H OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                            6.21                                                                             C(CH.sub.3).sub.2OH                                                                    6-F   H OCH.sub.3                                                                         CH.sub.3                                                                            CH O                                            6.22                                                                             C(CH.sub.3).sub.2OH                                                                    6-F   H CH.sub.3                                                                          CH.sub.3                                                                            CH O                                            6.23                                                                             C(CH.sub.3).sub.2OH                                                                    6-F   H CH.sub.3                                                                          OCHF.sub.2                                                                          CH O                                            6.24                                                                             C(CH.sub.3).sub.2OH                                                                    6-F   H CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                            6.25                                                                             C(CH.sub.3).sub.2OH                                                                    6-F   H OCH.sub.3                                                                         N(CH.sub.3).sub.2                                                                   N  O                                            6.26                                                                             C(CH.sub.3).sub.2OH                                                                    6-F   H OCH.sub.3                                                                         OCH.sub.3                                                                           N  O                                            6.27                                                                             C.sub.6 H.sub.5                                                                        6-F   H OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                            6.28                                                                             C.sub.6 H.sub.5                                                                        6-F   H CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                            6.29                                                                             C.sub.6 H.sub.5                                                                        6-F   H OCH.sub.3                                                                         OCH.sub.3                                                                           N  O                                            6.30                                                                             C.sub.6 H.sub.5                                                                        6-F   H OCH.sub.3                                                                         N(CH.sub.3).sub.2                                                                   N  O                                            6.31                                                                             2-thienyl                                                                              6-F   H OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                            6.32                                                                             2-thienyl                                                                              6-F   H CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                            6.33                                                                             2-furyl  6-F   H OCH.sub.3                                                                         OCH.sub.3                                                                           CH O                                            6.34                                                                             2-furyl  6-F   H CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                            6.35                                                                             CH.sub.3 H     H CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                            6.36                                                                             CH.sub.3 H     H CH.sub.3                                                                          OCH.sub.3                                                                           CH O                                            6.37                                                                             H        H     H CH.sub.3                                                                          OCH.sub.3                                                                           CH O                                            6.38                                                                             CH.sub.3 6-COOCH.sub.3                                                                       H CH.sub.3                                                                          OCH.sub.3                                                                           CH O                                            6.39                                                                             CH.sub.3 6-COOCH.sub.3                                                                       H CH.sub. 3                                                                         OCH.sub.3                                                                           N  O                                            6.40                                                                             CH.sub.3 6-CF.sub.3                                                                          H CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                            6.41                                                                             CH.sub.3 6-CF.sub.3                                                                          H CH.sub.3                                                                          OCH.sub.3                                                                           CH O                                            6.42                                                                             CH.sub.3 6-OCH.sub.3                                                                         H CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                            6.43                                                                             CH.sub.3 6-OCH.sub.3                                                                         H CH.sub.3                                                                          OCH.sub.3                                                                           CH O                                            6.44                                                                             CH.sub.3 6-OCHF.sub.2                                                                        H CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                            6.45                                                                             CH.sub.3 6-OCHF.sub.2                                                                        H CH.sub.3                                                                          OCH.sub.3                                                                           CH O                                            6.46                                                                             CH.sub.3 6-CH.sub.3                                                                          H CH.sub.3                                                                          OCH.sub.3                                                                           N  O                                            6.47                                                                             CH.sub.3 6-CH.sub.3                                                                          H CH.sub.3                                                                          OCH.sub.3                                                                           CH O                                            __________________________________________________________________________

Example 2 Formulation examples for compounds of formula I or mixturesthereof with herbicides (persentages are by weight)

    ______________________________________                                        (a) Wettable powders                                                                              (a)     (b)     (c)                                       ______________________________________                                        Compound of formula I                                                                             20%     60%     0.5%                                      sodium lignosulfonate                                                                             5%      5%      5%                                        sodium laurylsulfate                                                                              3%      --      --                                        sodium diisobutylnaphthalenesulfonate                                                             --      6%      6%                                        octylphenol polyethylene glycol ether                                                             --      2%      2%                                        (7-8 moles of ethylene oxide)                                                 highly dispersed silicid acid                                                                     5%      27%     27%                                       kaolin              67%     --      --                                        sodium chloride     --      --      59.5%                                     ______________________________________                                    

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, affording wettablepowders which can be diluted with water to give suspensions of thedesired concentration.

    ______________________________________                                        (b) Emulsifiable concentrates                                                                         (a)    (b)                                            ______________________________________                                        Compound of formula I   10%    1%                                             octylphenol polyethylene glycol ether                                                                  3%    3%                                             (4-5 moles of ethylene oxide)                                                 calcium dodecylbenzenesulfonate castor                                                                 4%    4%                                             oil polyglycol ether (36 moles of                                             ethylene oxide)                                                               cyclohexanone           30%    10%                                            xylene mixture          50%    79%                                            ______________________________________                                    

Emulsions of any required concentration can be obtained from thisconcentrate by dilution with water.

    ______________________________________                                        (c) Dusts           (a)     (b)                                               ______________________________________                                        Compound of formula I                                                                              0.1%    1%                                               talcum              99.9%   --                                                kaolin              --      99%                                               ______________________________________                                    

Dusts which are ready for use are obtained by mixing the activeingredient with the carriers, and grinding the mixture in a suitablemill.

    ______________________________________                                        (d) Extruder granulate                                                                            (a)    (b)                                                ______________________________________                                        Compound of formula I                                                                             10%    1%                                                 sodium lignosulfonate                                                                              2%    2%                                                 carboxymethylcellulose                                                                             1%    1%                                                 kaolin              87%    96%                                                ______________________________________                                    

The active ingredient is mixed and ground with the adjuvants, and themixture is subsequently moistened with water. The mixture is extrudedand then dried in a stream of air.

    ______________________________________                                        (e) Coated granulate                                                          ______________________________________                                        Compound of formula I                                                                           3%                                                          polyethylene glycol 200                                                                         2%                                                          kaolin            94%                                                         ______________________________________                                    

The finely ground active ingredient is uniformly applied, in a mixer, tothe kaolin moistened with polyethylene glycol. Non-dusty coatedgranulates are obtained in this manner.

    ______________________________________                                        (f) silicone concentrate                                                                             (a)     (b)                                            ______________________________________                                        Compound of formula I  40%     5%                                             ethylene glycol        10%     10%                                            nonylphenol polyethylene glycol ether                                                                 6%     1%                                             (15 moles of ethylene oxide)                                                  sodium lignosulfonate  10%     5%                                             carboxymethylcellulose  1%     1%                                             37% aqueous formaldehyde solution                                                                    0.2%    0.2%                                           silocone oil in the form of a 75%                                                                    0.8%    0.8%                                           aqueous emulsion                                                              water                  32%     77%                                            ______________________________________                                    

The finely ground active ingredient is intimately mixed with theadjuvants, giving a suspension concentrate from which suspensions of anydesired concentration can be obtained by dilution with water.

    ______________________________________                                        (g) Salt solution                                                             ______________________________________                                        Compound of formula I  5%                                                     isopropylamine         1%                                                     octylphenol polyethylene glycol ether                                                                3%                                                     (78 moles of ethylene oxide)                                                  water                  91%                                                    ______________________________________                                    

BIOLOGICAL EXAMPLES Example 3: Preemergence herbicidal action

Plastic pots are filled with expanded vermiculite (density: 0.135 g/cm³,water-absorbing capacity: 0.565 l/l). After the non-adsorptivevermiculite has been saturated with an aqueous emsulion in deionisedwater which contains that test compound in concentration of 70.8 ppm,seeds of the following plants are sown on the surface: Nasturtiumofficinalis, Agrostis tenuis, Stellaria media and Digitaria sanguinalis.The pots are then kept in a climatic chamber at 20° C., an illuminationof about 20 lux and a relative humidity of 70%. During the germinatingphase of 4 to 5 days, the pots are covered with lightpermeable materialand watered with deionised water to increase the local humidity. Afterthe 5th day, 0.5% of a commercial liquid fertiliser (Greenzit®) is addedto the water. The test is evaluated 12 days after sowing and the actionon the plants is assessed according to the following rating:

1: plants have not emerged or are totally withered

2-3: very pronounced action

4-6: medium action

7-8: weak action

9: no action (as untreated controls).

    ______________________________________                                        Preemergence action:                                                          Concentration of the test compound emulsion: 70.8 ppm                         Test plant                                                                    Compound Nasturtium                                                                              Stellaria  Agrostis                                                                             Digitaria                                ______________________________________                                        5.1      1         1          1      1                                        5.2      1         2          1      2                                        5.3      2         2          1      3                                        5.5      2         3          2      4                                         5.17    2         2          2      3                                         5.33    1         2          1      2                                        ______________________________________                                    

Example 4: Postemergence herbicidal action (contact action)

A number of weeds and cultivated plants, both monocots and dicots, aresprayed postemergence, in the 4- to 6-leaf stage, with an aqueousdispersion of test compound at a rate of application of 4 kg a.i./ha,and then kept at 24°-26° and 46-60% relative humidity. The test isevaluated 15 days after treatment using the same rating as in thepreemergence test.

    ______________________________________                                        Postemergence action                                                          Compound                                                                              Avena    Solanum Sinapis                                                                              Stellaria                                                                            Phaseolus                              ______________________________________                                        5.1     6        2       2      4      2                                      5.33    6        2       3      5      3                                      ______________________________________                                    

Example 5: Inhibition of sprouting is stored potatoes

A number or commercially available potatoes of the "Urgenta" variety,without sprouts, are washed and dried. The potatoes are then immersed inemulsions of the compounds to be tested in different concentrations,placed on filter paper in plastic dishes, and kept in the dark at14°-21° C. and 50% relative humidity. Evaluation is made 34 days afterapplication.

The percentage weight loss of the tubers and the weight of the sproutscompared with untreated controls are simultaneously determined.

In the test, the compounds of the invention inhibit sproutingcompletely. At the same time, the weight loss of the potatoes is lessthan 10% of that of the controls.

Example 6: Growth inhibition of tropical cover crops

The test plants (centrosema plumieri and centrosema pubescens) arereared until fully grown and then cut back to a height of 60 cm. Theplants are sprayed 7 days later with an aqueous emulsion of the testcompound. The test plants are kept at 70% relative humidity and 6000 luxartificial light for 14 hours per day, at day temperatures of 27° C. andnight temperatures of 21° C. The test is evaluated 4 weeks afterapplication by assessing and weighing the new growth compared withcontrols and by determining the phytotoxicity.

In this test a marked reduction in new growth of the plants treated withcompounds of the formula I is observed (less than 20% of the new growthof untreated control plants), without damage being caused to the testplants.

What is claimed is:
 1. N-phenylsulfonyl-N'-triazinylurea of the formula##STR23## wherein A is a radical of the formula --C.tbd.C--R,m is 1 or2, Z is oxygen or sulfur, R is hydrogen; branched or unbranched C₁ -C₉alkyl which is unsubstituted or substituted by halogen, hydroxyl, C₁ -C₄alkoxy, C₁ -C₄ alkylthio, C₁ -C₄ haloalkoxy, C₃ -C₉ cycloalkyl, cyano,--COOR₆, --CONR₇ R₈ or by phenyl which is in turn unsubstituted orsubstituted by halogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, nitro, cyano ortrifluoromethyl; or is C₃ -C₉ cycloalkyl which is unsubstituted orsubstituted by halogen, hydroxyl, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄alkylthio, cyano, --COOR₆, --CONR₇ R₈ ; or is phenyl or phenylsubstituted by halogen, nitro, cyano, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁-C₄ alkylthio, trifluoromethyl, --COOR₆ or --CONR₇ R₈ ; or is a 5- or6-membered heterocyclic ring selected from the group consisting offuran, thiophene, pyrrole, pyrazole, triazole, pyridine, pyrimidine,pyridazine, triazine, thiazole, oxazole, thiadiazole and oxadiazole,which is unsubstituted or substituted by halogen, C₁ -C₄ alkyl, C₁ -C₄alkoxy, --COOR₆ or --CONR₇ R₈, R₁ is hydrogen, halogen, C₁ -C₅ alkyl, C₂-C₅ alkyl, C₂ -C₅ alkenyl or a radical --Y--R₅, R₂ is hydrogen, halogen,C₁ -C₅ alkyl, C₂ -C₅ alkenyl, C₁ -C₄ haloalkyl, or a radical --Y--R₅,--COOR₆, --NO₂ or --CO--NR₇ --R₈, R₃ and R₄, each independently of theother, are hydrogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ alkylthio, C₁-C₄ haloalkyl, C₁ -C₄ haloalkoxy, C₁ -C₄ haloalkylthio, halogen, C₂ -C₅alkoxyalkyl, --NR₉ R₁₀ or --O--CH₂ --CH₂ --NR₉ R₁₀, R₅ and R₆, eachindependently of the other, are C₁ -C₅ alkyl, C₂ -C₅ alkenyl or C₂ -C₆alkynyl, C₁ -C₅ haloalkyl, C₂ -C₅ haloalkenyl or C₂ -C₆ alkoxyalkyl, R₇and R₈, each independently of the other, are hydrogen, C₁ -C₅ alkyl, C₂-C₅ alkenyl or C₂ -C₆ alkynyl, R₉ is hydrogen, methyl or ethyl, R₁₀ ishydrogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, methoxymethyl, cyanomethyl,cyanoethyl, C₃ -C₅ alkenyl or C₃ -C₆ alkynyl, and Y is oxygen, sulfur, asulfinyl or sulfonyl bridge, or a salt thereof.
 2. A compound accordingto claim 1, wherein Z is oxygen and m is 1, and R₃ and R₄ togethercontain not more than 4 carbon atoms.
 3. A compound according to claim2, wherein A is in the 2- or 3-position to the sulfonyl group, R₁ ishydrogen and R₂ is in the 5- or 6-position to the sulfonyl group.
 4. Acompound according to claim 3, wherein R₂ is hydrogen, chlorine,fluorine, nitro, trifluoromethyl, C₁ -C₄ haloalkoxy, C₁ -C₄alkoxycarbonyl or C₁ -C₄ alkoxy, each of R₃ and R₄ is hydrogen, C₁ -C₄alkyl, C₁ -C₄ alkoxy, C₁ -C₄ alkylthio, dialkylamino, C₁ -C₃ haloalkoxy,halogen or alkoxyalkyl, R is hydrogen or branched or unbranched C₁ -C₄alkyl which is unsubstituted or substituted by halogen, hydroxyl,methoxy, methylthio, C₁ -C₄ haloalkoxy, cyclopropyl, cyano,methoxycarbonyl, or is phenyl, pyridyl, thienyl or furyl; and R is inthe 2- or 3-position. 5.N-[2-(propyn-1-yl)-6-chlorophenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureaaccording to claim
 1. 6.N[2-(propyn-1-yl)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureaaccording to claim
 1. 7. A herbicidal and plant growth-inhibitingcomposition which contains at least oneN-phenylsulfonyl-N'-triazinylurea according to claim 1, together withcarriers and/or other adjuvants.
 8. A method of controlling undesiredplant growth which comprises applying to said plant growth aherbicidally effective amount of a N-phenylsulfonyl-N'-triazinylureaaccording to claim
 1. 9. A method of inhibiting plant growth, whichcomprises applying to said plants a growth inhibiting effective amountof a N-phenylsulfonyl-N'-triazinylurea according to claim
 1. 10. Amethod according to claim 8 for selectively controlling weeds pre- orpostemergence in crops of useful plants.
 11. A method according to claim9 for inhibiting plant growth beyond the 2-leaf stage preemergence. 12.A method according to claim 9 for inhibiting the growth of leguminouscover crops.
 13. A method according to claim 9 for inhibiting thesprouting of stored potatoes.
 14. A method according to claim 10,wherein the crops of useful plants are cereals, cotton, soybeans, maizeand rice.